Hexafluorosilicic Acid as a Novel Reagent for the Desilylation of Silylacetylenes: Application in Sequential Sonogashira Coupling and Click Reaction

Abstract Hexafluorosilicic acid was utilized as a novel, cheap, readily available, and environmentally benign alternative reagent for the desilylation of 1-trimethylsilylacetylenes. The applicability of the aqueous solution of the hexafluorosilicic acid was demonstrated in the sequential coupling of...

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Veröffentlicht in:Synthesis (Stuttgart) 2017-06, Vol.49 (11), p.2374-2388
Hauptverfasser: Sinai, Ádám, Mészáros, Ádám, Balogh, Ádám, Zwillinger, Márton, Novák, Zoltán
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract Hexafluorosilicic acid was utilized as a novel, cheap, readily available, and environmentally benign alternative reagent for the desilylation of 1-trimethylsilylacetylenes. The applicability of the aqueous solution of the hexafluorosilicic acid was demonstrated in the sequential coupling of aryl halides and ethynyltrimethylsilane to afford internal acetylenes, benzofurans, and triazoles in one-pot Sonogashira–Sonogashira­ and Sonogashira–CuAAC reactions.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588981